Asymmetric Synthesis of α,α-Disubstituted Amino Acids by Cycloaddition of ( E )-Ketonitrones with Vinyl Ethers - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2014

Asymmetric Synthesis of α,α-Disubstituted Amino Acids by Cycloaddition of ( E )-Ketonitrones with Vinyl Ethers

Résumé

Original acyclic (E)-α,α-dialkylketonitrones bearing a chiral auxiliary on their nitrogen atom were synthesized and successfully employed for the asymmetric synthesis of α,α-disubstituted amino acids using regio- and stereocontrolled 1,3-dipolar cycloaddition reactions with vinyl ethers. N-Glycosyl chiral auxiliaries were found to provide excellent exo- and π-facial stereocontrol. The obtained enantiopure cycloadducts were selectively transformed into functional α,α-disubstituted amino acids and related β-peptides through the highly regioselective opening of an intermediate quaternary anhydride.

Domaines

Chimie
Fichier non déposé

Dates et versions

hal-01652164 , version 1 (30-11-2017)

Identifiants

Citer

Xiaofei Zhang, Pascale Cividino, Jean-François Poisson, Pavlo Shpak-Kraievskyi, Mathieu Y. Laurent, et al.. Asymmetric Synthesis of α,α-Disubstituted Amino Acids by Cycloaddition of ( E )-Ketonitrones with Vinyl Ethers. Organic Letters, 2014, 16 (7), pp.1936-1939. ⟨10.1021/ol500483t⟩. ⟨hal-01652164⟩
43 Consultations
0 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More